I think the big thing that you're missing is that "great execution" doesn't end at building a great product. And PR is not a marketing strategy.

If you want to avoid this experience again, choose an idea that:

1) Has a broad-content SEO strategy (think StackOverflow and Yelp). New/valuable content gets created every day.

2) Has a channel for "buying" customers with economics that work. Plenty of people make adwords work. Plenty of others can afford salespeople. Find a market where people are succeeding at buying customers and compete in it.

3) Has a viral loop. Think Farmville or Groupon. Why is it in your customers best interest to evangelize your product? They can be motivated by psychology or $.

It's not about a "great idea". Well, it can be. But look at all of the shitty products that are minting money! You can aim for a "addictive/amazing" product (and should), but it better be backed by sound customer acquisition economics for the (likely) case that your product is merely good.

About your launch day: You expect to blow it out on launch day? That's not a reasonable expectation. It's a marathon not a 100 yard dash.

edit: TechCrunch should not be a goal. At YC there's a word for the period after TechCrunch coverage... "The trough of despair". It's the period of time after TC where your traffic flatlines and you realize that TC isn't a springboard to anything-- it's just the first step (if you're lucky) on a really long slog to building a business.

How many acquisition channels has he investigated? Adwords is a pretty expensive one that only works for certain types of products. He tried that. What else? Hard to comment on his actual idea. Assuming he has competition, that means someone has figured out how to find customers in a scalable way.

Maybe his idea, with a 10 degree pivot, could be a viral/SEO sensation. I've no idea.

"Specifically, he says that the software business is undergoing radical changes because technical competence is no longer a scarce commodity: with open source tools, an increasing supply of trained programmers, and the explosion of cost-lowering innovations for creating and marketing software on the Internet, things which were previously the purview of a technical elite are now within what talented teenagers can cook up from their kitchen table."

A good web app is really only the "entrance fee" to the more challenging (and longer term) game of building a business.

I don't know, I've had this discussion a few times, about the differences between PR and marketing. Ppl at my company say they do 'PR' and 'because it's good PR' but I'm not interested in PR, I'm interested in sales. Marketing leads to sales, it leads people to learn about your product and to want to buy that product; PR just leads to people liking your company, which is only a small factor in the buying decision, and only after they've already decided they want to buy. But, and here's the rub, being in 'marketing' is not cool, it's full of negative connotations, it's hard and full of elbow grease; PR is about writing lofty prose from your well-lit corner office before going on a 2-hour lunch with some journalist. So 'doing PR' is something people want to do, 'doing marketing' not. (which makes that those who want to do marketing, and are not afraid of it, can make huge hits).